Buccleuch Estates Ltd, which owns more than 10,000ha of hardwood and softwood forest and woodlands, was fined at Dumfries Sheriff Court.
The court heard that victim Ross Findlay, who had learning difficulties, died after being struck in the head and body by a 36m tall tree which had been uprooted and knocked over by another tree being felled.
He had been acting as a signalman between two other workers when the incident occurred. They were felling large spruce and larch trees at Bogrie Wood near Drumlanrig Castle.
An investigation by the Health and Safety Executive found the estate failed to conduct a suitable and sufficient risk assessment, implement a safe system of work or provide adequate information or training.
The court heard that Mr Findlay should have been at least two tree lengths away from the tree being felled but due to his learning difficulties he did not always appreciate distances and was well within the zone when the accident happened.
“A system of waves and nods is not a safe way to manage the felling of large, heavy trees and put all three workers at unnecessary risk,” said HSE inspector Aileen Jardine.
“This informal and unsafe way of working had been in place unchallenged and not updated for over 15 years with the estate making no efforts to follow industry safety guidelines or to even accurately assess the risks its workers faced.”